Vacation rentals in Oakland

The Original Hob

We have the Original Hob and Molly (separate listing) overlooking our creek at the point of 7 little waterfalls for your sleeping and hangout pleasure! A shared sweet kitchen and bath completes the 3 small structures. Full bath plus an outdoor shower makes for great accommodations. We're within 5 miles of State Parks and Deep Creek Lake. Come see the Garrett County stars, hear the creek and birds and be a million miles from where you are. Friendly dogs are welcomed -see "other things to note".

Mountain Air Oasis with Hot Tub

Relax with the whole family or friends at this peaceful private 2 acre property, close to Maryland's natural attractions! A family-friendly three bedroom home 1,380 sq. ft secluded in a rural neighborhood. Wildlife to watch and enjoy! Relax with a campfire or soak in the hot tub! We are located approximately 30 minutes from Swallow Falls State Park, Deep Creek Lake, and Black Water Falls State Park. We are also within 10 minutes of two wedding venues (The White Barn, and Twin Tales Event Farm).

The Falls Cabin ↟↟ secluded log cabin in the woods

hello, and welcome to @thefallscabin! we are so happy you’re here. :) the falls cabin sits quietly tucked away on 11 wooded acres, located just minutes from deep creek lake, swallow falls state park, and wisp resort. it is the perfect spot for getting away from the noise – but being close to it all. the cabin is equipped with brand-new furniture, mattresses, etc. follow us @thefallscabin for more photos and progress as we continue to flip this lovely place into our modern, wooded oasis.

Wooded camp w/lake views/fire pit. Great location.

Cozy lake view camp in Deep Creek. Centrally located to all amenities. Open floor layout with full kitchen. Master bedroom has a Queen bed, master BR, closet, and lake view via sliding doors leading to the deck. Second bedroom features bunk beds (weight limit 165lbs) and a computer desk. Lastly, the 3rd BR contains a Full bed. There's also separate laundry room. Back deck overlooks Deep Creek Lake. Large firepit. Wireless internet, ROKU TV's, DVD, Wii gaming and Google Chromecast provided.

Spring is in the air at our Lake View Condo!

Centrally located 3 story condo on beautiful Deep Creek Lake. Come enjoy all 4 seasons on the lake. Ski Wisp is 5 mins away. Walking distance to shops and restaurants. 2 bedrooms and 2 full baths. 3rd floor is the loft with bunk beds. Brand new kitchen with new cabinets, granite and stainless appliances. Cathedral ceilings throughout. Wood burning fireplace. Large deck with a beautiful lake view. Come relax and play on the lake or the mountain. Enjoy everything Deep Creek has to offer!

Dancing Bears

***PLEASE NO PETS*** Meticulously maintained authentic log cabin in the woods getaway! Our 800 sf cabin has two bedrooms, one bathroom and large bonus 3rd bedroom/loft area (queen bed, two cots, kids' play area, TV and home office space). Our location is secluded yet conveniently located to all of the activities Deep Creek Lake has to offer. The property backs up to 65 wooded acres at the end of a private road. Peaceful setting with a stream, fire pit, picnic table, and horse shoe pit.

SUGARBUSH - Sweet Serenity Tiny House

Welcome to SUGARBUSH! "Suga" is a 450 sq. ft. custom built tiny house. She will comfortably accommodate 2 adults or a family with 2 small children. AGE REQUIREMENT to book this space is 25+. At this time we DO NOT allow pets. Suga sits on a 3+ acre lot that use to be used for cross country skiing. She got her name from two trails, Sugarbush Run and Sugarbush Shortcut that ran through the lot! We welcome you to stay and enjoy our wonderful little getaway here in Pleasant Valley.

Deep Creek Lake Cozy Cottage (Dog Friendly)

Bright, light, newly renovated lake cottage situated on a wooded lot, with cozy fireplace, large deck areas-front and back (with gas firepit), and 3 bedrooms with french doors that open to outdoor space. Community lakefront with private lake frontage just a short walk away. Enjoy swimming and water sports from the dock and lakefront area, snow skiing, sledding, tubing and snowboarding at Wisp Resort, hiking, Swallow Falls State Park and Deep Creek Lake State Park.

Boulder Ridge Cabin, close to Deep Creek, Maryland

Boulder Ridge Cabin is surrounded by woods, but within 15 minutes of Deep Creek Lake, swimming, boating, hiking, shopping, restaurants, Wisp Resort with skiing, snowboarding, mountain coaster, whitewater rafting at Adventure Sports Center International, rock climbing, hiking. Swallow Falls State Park and Herrington Manor State Park are about 15 minutes drive. Piney Mountain State Forest is within walking distance. Mountain biking and fishing are also close by.

Lake View Loft Lodge on Deep Creek Lake

Seconds away from the lake, Trader's Coffee House, Brenda's Pizzeria, High Mountain Sports, and minutes away from Wisp Ski Resort, entertainment, shopping, food, and anything else you could want. Just eight miles south of Deep Creek Lake is historic Oakland, MD. Oakland is known for its small-town feel with local restaurants, small businesses, and popular festivals. Taking the time to visit Downtown Oakland is a must-see on your to-do list at Deep Creek Lake.

Cheerful cottage 2 minutes from Deep Creek Lake

Just the right size and location for enjoying all Deep Creek Lake has to offer- including scenic hikes on many nearby trails, skiing at Wisp, or just enjoying time on the lake amongst bustling lake life. Then retreat back to our quaint cottage and enjoy time together. You will love our place because of its coziness, location, cleanliness, affordability and perfect size for a single family stay. *bathroom is in the bedroom *we have parking for a boat*

Pet friendly-Cottage in the Woods

Tucked conveniently between Swallow Falls State Park and Deep Creek Lake, this recently renovated 2 bd cottage has everything you need for a weekend getaway or a much needed week(s) long vacation!  Inside you will find a completely stocked kitchen, open living/dining area,  full size bathroom, 2 bedrooms and a cozy nook with sleeper sofa and desk.  Relax and unwind in the spacious backyard or charming balcony. *pets stay free